Highly diastereoselective reaction of a chiral, non-racemic amide enolate with (S)-glycidyl tosylate. Synthesis of the orally active HIV-1 protease inhibitor L-735,524

D Askin, KK Eng, K Rossen, RM Purick, KM Wells…

Index: Askin, David; Eng, Kan K.; Rossen, Kai; Purick, Robert M.; Wells, Kenneth M.; et al. Tetrahedron Letters, 1994 , vol. 35, # 5 p. 673 - 676

Full Text: HTML

Citation Number: 151

Abstract

Download full text in PDF Opens in a new window. Article suggestions will be shown in a dialog on return to ScienceDirect. ... Please enable JavaScript to use all the features on this page. ... Reaction of chiral amide enolate Li-1 with (S)-glycidyl tosylate 11 affords the epoxide 3 in 72% yield with high diastereoselectivity. Epoxide 3 is converted to the orally-active HIV-1 protease inhibitor L-735,524 in 71% isolated yield. ... J. Org. Chem., 57 (1992), pp. 2771–2773 ...